A dark brown crew-neck sweater and black chinos are a smart combo to keep in your current casual routine. For something more on the dressier end to complement your look, complement this ensemble with a pair of black suede chelsea boots. Dressing warmly is the key to surviving below-freezing temps, but this ensemble is a practical illustration that this can also be done with style. As you're getting to your 30s, you want to start dressing more like a mature gentleman. That's when combos like this are a foolproof option.